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The Bouncy Castle Java APIs for CMS, PKCS, EAC, TSP, CMP, CRMF, OCSP, and certificate generation. This jar contains APIs for JDK 1.5 to JDK 1.8. The APIs can be used in conjunction with a JCE/JCA provider such as the one provided with the Bouncy Castle Cryptography APIs.
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package org.bouncycastle.openssl;

import java.io.ByteArrayOutputStream;
import java.io.IOException;
import java.io.OutputStream;
import java.security.NoSuchAlgorithmException;
import java.security.NoSuchProviderException;
import java.security.PrivateKey;
import java.security.Provider;
import java.security.SecureRandom;
import java.security.Security;

import org.bouncycastle.asn1.ASN1ObjectIdentifier;
import org.bouncycastle.asn1.nist.NISTObjectIdentifiers;
import org.bouncycastle.asn1.pkcs.EncryptedPrivateKeyInfo;
import org.bouncycastle.asn1.pkcs.PKCSObjectIdentifiers;
import org.bouncycastle.asn1.pkcs.PrivateKeyInfo;
import org.bouncycastle.openssl.jcajce.JceOpenSSLPKCS8EncryptorBuilder;
import org.bouncycastle.operator.OperatorCreationException;
import org.bouncycastle.operator.OutputEncryptor;
import org.bouncycastle.util.io.pem.PemGenerationException;
import org.bouncycastle.util.io.pem.PemObject;
import org.bouncycastle.util.io.pem.PemObjectGenerator;

public class PKCS8Generator
    implements PemObjectGenerator
{
    public static final ASN1ObjectIdentifier AES_128_CBC = NISTObjectIdentifiers.id_aes128_CBC;
    public static final ASN1ObjectIdentifier AES_192_CBC = NISTObjectIdentifiers.id_aes192_CBC;
    public static final ASN1ObjectIdentifier AES_256_CBC = NISTObjectIdentifiers.id_aes256_CBC;

    public static final ASN1ObjectIdentifier DES3_CBC = PKCSObjectIdentifiers.des_EDE3_CBC;

    public static final ASN1ObjectIdentifier PBE_SHA1_RC4_128 = PKCSObjectIdentifiers.pbeWithSHAAnd128BitRC4;
    public static final ASN1ObjectIdentifier PBE_SHA1_RC4_40 = PKCSObjectIdentifiers.pbeWithSHAAnd40BitRC4;
    public static final ASN1ObjectIdentifier PBE_SHA1_3DES = PKCSObjectIdentifiers.pbeWithSHAAnd3_KeyTripleDES_CBC;
    public static final ASN1ObjectIdentifier PBE_SHA1_2DES = PKCSObjectIdentifiers.pbeWithSHAAnd2_KeyTripleDES_CBC;
    public static final ASN1ObjectIdentifier PBE_SHA1_RC2_128 = PKCSObjectIdentifiers.pbeWithSHAAnd128BitRC2_CBC;
    public static final ASN1ObjectIdentifier PBE_SHA1_RC2_40 = PKCSObjectIdentifiers.pbeWithSHAAnd40BitRC2_CBC;

    private PrivateKeyInfo key;
    private OutputEncryptor outputEncryptor;
    private JceOpenSSLPKCS8EncryptorBuilder encryptorBuilder;

    /**
     * Constructor for an unencrypted private key PEM object.
     *
     * @param key private key to be encoded.
     * @deprecated use JcaPKCS8Generator
     */
    public PKCS8Generator(PrivateKey key)
    {
        this.key = PrivateKeyInfo.getInstance(key.getEncoded());
    }

    /**
     * Constructor for an encrypted private key PEM object.
     *
     * @param key       private key to be encoded
     * @param algorithm encryption algorithm to use
     * @param provider  name of provider to use
     * @throws NoSuchProviderException  if provider cannot be found
     * @throws NoSuchAlgorithmException if algorithm/mode cannot be found
     *  @deprecated  use JcaPKCS8Generator
     */
    public PKCS8Generator(PrivateKey key, ASN1ObjectIdentifier algorithm, String provider)
        throws NoSuchProviderException, NoSuchAlgorithmException
    {
        Provider prov = Security.getProvider(provider);

        if (prov == null)
        {
            throw new NoSuchProviderException("cannot find provider: " + provider);
        }

        init(key, algorithm, prov);
    }

    /**
     * Constructor for an encrypted private key PEM object.
     *
     * @param key       private key to be encoded
     * @param algorithm encryption algorithm to use
     * @param provider  provider to use
     * @throws NoSuchAlgorithmException if algorithm/mode cannot be found
     * @deprecated  use JcaPKCS8Generator
     */
    public PKCS8Generator(PrivateKey key, ASN1ObjectIdentifier algorithm, Provider provider)
        throws NoSuchAlgorithmException
    {
        init(key, algorithm, provider);
    }

    /**
     * Base constructor.
     */
    public PKCS8Generator(PrivateKeyInfo key, OutputEncryptor outputEncryptor)
    {
        this.key = key;
        this.outputEncryptor = outputEncryptor;
    }

    private void init(PrivateKey key, ASN1ObjectIdentifier algorithm, Provider provider)
        throws NoSuchAlgorithmException
    {
        this.key = PrivateKeyInfo.getInstance(key.getEncoded());
        this.encryptorBuilder = new JceOpenSSLPKCS8EncryptorBuilder(algorithm);

        encryptorBuilder.setProvider(provider);
    }

    /**
     * @deprecated ignored in the updated case.
     */
    public PKCS8Generator setSecureRandom(SecureRandom random)
    {
        encryptorBuilder.setRandom(random);

        return this;
    }

    /**
     * @deprecated ignored in the updated case.
     */
    public PKCS8Generator setPassword(char[] password)
    {
        encryptorBuilder.setPasssword(password);

        return this;
    }

    /**
     * @deprecated ignored in the updated case.
     */
    public PKCS8Generator setIterationCount(int iterationCount)
    {
        encryptorBuilder.setIterationCount(iterationCount);

        return this;
    }

    public PemObject generate()
        throws PemGenerationException
    {
        try
        {
            if (encryptorBuilder != null)
            {
                outputEncryptor = encryptorBuilder.build();
            }
        }
        catch (OperatorCreationException e)
        {
            throw new PemGenerationException("unable to create operator: " + e.getMessage(), e);
        }

        if (outputEncryptor != null)
        {
            return generate(key, outputEncryptor);
        }
        else
        {
            return generate(key, null);
        }
    }

    private PemObject generate(PrivateKeyInfo key, OutputEncryptor encryptor)
        throws PemGenerationException
    {
        try
        {
            byte[] keyData = key.getEncoded();

            if (encryptor == null)
            {
                return new PemObject("PRIVATE KEY", keyData);
            }

            ByteArrayOutputStream bOut = new ByteArrayOutputStream();

            OutputStream cOut = encryptor.getOutputStream(bOut);

            cOut.write(key.getEncoded());

            cOut.close();

            EncryptedPrivateKeyInfo info = new EncryptedPrivateKeyInfo(encryptor.getAlgorithmIdentifier(), bOut.toByteArray());

            return new PemObject("ENCRYPTED PRIVATE KEY", info.getEncoded());
        }
        catch (IOException e)
        {
            throw new PemGenerationException("unable to process encoded key data: " + e.getMessage(), e);
        }
    }
}